L-alanin
(S)-2-chloropropanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; nitrosylchloride In water at 0℃; for 1h; Temperature; | 94% |
With hydrogenchloride; sodium nitrite In water at -5 - 20℃; | 89% |
Stage #1: L-alanin With hydrogenchloride; tartaric acid; iron(II) chloride In water for 1h; Stage #2: With sodium nitrite In water at 0℃; for 4h; Reagent/catalyst; | 85.4% |
A
(S)-2-chloropropanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane; water at 50℃; for 24h; Inert atmosphere; | A 91% B 93% |
A
(S)-2-chloropropanoic acid
C
(R)-2-chloropropionic acid
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane at 50℃; for 8h; Inert atmosphere; Resolution of racemate; | A n/a B 91% C n/a |
(S)-2-chloropropanoic acid
Conditions | Yield |
---|---|
With lithium hydroxide; dihydrogen peroxide In tetrahydrofuran at 0℃; for 0.25h; | 86% |
(+)-ethyl 2-chloropropionate
(S)-2-chloropropanoic acid
Conditions | Yield |
---|---|
With sodium hydroxide In water | 85% |
L-alanine
(S)-2-chloropropanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite at 0℃; for 20h; | 71% |
(S)-2-Chlorpropionsaeure-isobutylester
(S)-2-chloropropanoic acid
Conditions | Yield |
---|---|
With potassium hydroxide In water at 0℃; | 59% |
(2R,3S)-(+)-3-chlorobutane-2-ol
(S)-2-chloropropanoic acid
Conditions | Yield |
---|---|
With potassium hydroxide; bromine at 50℃; |
Conditions | Yield |
---|---|
subtilisin In water at 30℃; Kinetics; | |
With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; esterase from Pseudomonas fluorescens In water at 25℃; pH=7.20; Enzyme kinetics; | |
With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; lipase from Ophiostoma piliferum In water at 25℃; pH=7.20; Enzyme kinetics; | |
With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; lipase from Bacillus thermocatenulanatus In water at 40℃; pH=7.20; Enzyme kinetics; |
(RS)-1-Pentylpropynyl (L)-2-chloropropanoate
A
(S)-2-chloropropanoic acid
B
1-octyn-3-ol
C
(R)-1-Pentylpropynyl (L)-2-chloropropanoate
Conditions | Yield |
---|---|
With water; lipase CC lipase P; | |
With water; lipase CC Product distribution; or lipase P; | |
With lipase CC; water or lipase P; |
(RS)-Bicyclo<2.2.1>hept-2-yl (L)-2-chloropropanoate
A
(S)-2-chloropropanoic acid
B
(S)-Bicyclo[2.2.1]heptan-2-ol
C
(1R)-Bicyclo<2.2.1>hept-2-yl (L)-2-chloropropanoate
Conditions | Yield |
---|---|
With water; lipase CC lipase P; | |
With water; lipase CC Product distribution; lipase P; |
(R,S)-2-chloropropionic acid
(S)-2-chloropropanoic acid
1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-O-yl α-chloropropionate
A
(S)-2-chloropropanoic acid
B
(R)-2-chloropropionic acid
Conditions | Yield |
---|---|
With lithium hydroxide; dihydrogen peroxide In tetrahydrofuran for 0.5h; Yields of byproduct given. Title compound not separated from byproducts; |
2-chloro-propionic acid methyl ester
A
(S)-2-chloropropanoic acid
B
(R)-2-chloropropionic acid
Conditions | Yield |
---|---|
With Aspergillus niger lipase; sodium acetate buffer In diethyl ether Title compound not separated from byproducts; |
(S)-2-chloropropanoic acid
Conditions | Yield |
---|---|
With acetone; lithium chloride |
(S)-2-chloropropanoic acid
Conditions | Yield |
---|---|
With water; acetone; lithium chloride | |
With hydrogenchloride |
(S)-2-chloropropanoic acid
Conditions | Yield |
---|---|
With water at 25℃; |
(S)-2-chloropropanoic acid
Conditions | Yield |
---|---|
With chromic acid at 25℃; |
(S)-2-chloropropanoic acid
Conditions | Yield |
---|---|
ueber das Cinchoninsalz; |
(S)-2-chloropropanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; nitric acid; urea |
(S)-2-chloropropanoic acid
Conditions | Yield |
---|---|
With nitric acid; sodium nitrite |
hydrogenchloride
(2R)-2-(4-Toluenesulfonyloxy)propionic Acid
(S)-2-chloropropanoic acid
(2R)-2-(4-Toluenesulfonyloxy)propionic Acid
water
(S)-2-chloropropanoic acid
(2R)-2-(4-Toluenesulfonyloxy)propionic Acid
acetone
(S)-2-chloropropanoic acid
2-chloropropanal
A
(S)-2-chloropropanoic acid
B
(R)-2-chloropropionic acid
Conditions | Yield |
---|---|
With potassium permanganate; disodium hydrogenphosphate; tert-butyl alcohol for 0.0166667h; Title compound not separated from byproducts; |
2-Chloroacrylic acid
(S)-2-chloropropanoic acid
Conditions | Yield |
---|---|
With potassium phosphate buffer; Burkholderia sp. WS expressing reductase at 30℃; pH=7.1; |
(R,S)-2-chloropropionic acid
butan-1-ol
A
(S)-2-chloropropanoic acid
B
(R)-2-Chloro-propionic acid butyl ester
Conditions | Yield |
---|---|
With iron oxide-Candida rugosa (E.C.3.1.1.3) lipase In hexane at 30℃; for 168h; |
methyl-(S)-2-chloropropionate
(S)-2-chloropropanoic acid
Conditions | Yield |
---|---|
With sodium hydroxide |
(S)-2-chloropropanoic acid
isobutene
(S)-tert-butyl 2-chloropropanoate
Conditions | Yield |
---|---|
With hydrogen cation | 100% |
With hydrogen cation | 93% |
With sulfuric acid In dichloromethane at 20℃; for 48h; | 73% |
(S)-2-chloropropanoic acid
(S)-2-chloropropionyl chloride
Conditions | Yield |
---|---|
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 25℃; for 3h; | 99% |
With thionyl chloride for 4h; Product distribution / selectivity; Reflux; | 88.2% |
With benzoyl chloride at 150℃; | 52% |
Conditions | Yield |
---|---|
Stage #1: phenol With sodium hydroxide In water at 55℃; for 0.5h; Stage #2: (S)-2-chloropropanoic acid In water at 60℃; for 2h; Temperature; Reagent/catalyst; | 96.6% |
With water; sodium hydroxide at 50 - 70℃; Inert atmosphere; | 95% |
4-bromo-phenol
(S)-2-chloropropanoic acid
(2S)-2-(4-bromophenoxy)propanoic acid
Conditions | Yield |
---|---|
Stage #1: 4-bromo-phenol With sodium hydride In tetrahydrofuran for 1h; Heating / reflux; Stage #2: (S)-2-chloropropanoic acid In tetrahydrofuran for 120h; Heating / reflux; Stage #3: With hydrogenchloride In dichloromethane at 20℃; | 96.4% |
(S)-2-chloropropanoic acid
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
3-O-(D-1-carboxyethyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
Conditions | Yield |
---|---|
With sodium hydride In 1,4-dioxane at 65℃; for 3h; | 96% |
(S)-2-chloropropanoic acid
benzyl 2-acetamido-2-deoxy-5,6-O-isopropylidene-α-D-mannofuranoside
benzyl 2-acetamido-3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-α-D-mannofuranoside
Conditions | Yield |
---|---|
With sodium hydride In 1,4-dioxane at 65℃; for 3h; | 95% |
benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
(S)-2-chloropropanoic acid
benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside
Conditions | Yield |
---|---|
Stage #1: benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside With sodium hydride In 1,4-dioxane; mineral oil at 60℃; for 0.0833333h; Inert atmosphere; Stage #2: (S)-2-chloropropanoic acid In 1,4-dioxane; mineral oil at 60℃; for 16.5h; Inert atmosphere; | 94% |
Stage #1: benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside With sodium hydride In 1,4-dioxane at 95℃; for 2h; Stage #2: (S)-2-chloropropanoic acid In 1,4-dioxane at 60℃; for 3h; | 80% |
With sodium hydride In 1,4-dioxane at 65℃; | 80% |
Stage #1: benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside With sodium hydride In 1,4-dioxane; mineral oil at 70 - 95℃; for 1h; Williamson Ether Synthesis; Stage #2: (S)-2-chloropropanoic acid In 1,4-dioxane; mineral oil at 65 - 70℃; for 25h; Williamson Ether Synthesis; | 78% |
With sodium hydride In 1,4-dioxane; mineral oil at 0 - 70℃; for 3h; | 18 g |
(S)-2-chloropropanoic acid
1-isoquinolone
(R)-2-(1-oxoisoquinolin-2(1H)-yl)propanoic acid
Conditions | Yield |
---|---|
Stage #1: (S)-2-chloropropanoic acid With magnesium tert butanolate In tetrahydrofuran at 35℃; for 0.166667h; Inert atmosphere; Stage #2: With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere; Stage #3: 1-isoquinolone In tetrahydrofuran at 20 - 55℃; for 14.5h; Inert atmosphere; optical yield given as %ee; stereospecific reaction; | 94% |
(S)-2-chloropropanoic acid
(S)-3-[4-(2,6-Dichloro-benzyloxy)-phenyl]-2-(4-methoxy-benzylamino)-propionic acid methyl ester
N-[(S)-2-chloropropionyl]-N-p-methoxybenzyl-L-Tyr(2,6-dichlorobenzyl)-OMe
Conditions | Yield |
---|---|
Stage #1: (S)-2-chloropropanoic acid With trichloroacetonitrile; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: (S)-3-[4-(2,6-Dichloro-benzyloxy)-phenyl]-2-(4-methoxy-benzylamino)-propionic acid methyl ester With methyloxirane In tetrahydrofuran | 93% |
(S)-2-chloropropanoic acid
2-acetamido-4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-glucitol
2-acetamido-4,6-O-benzylidene-1,5-(benzyloxycarbonyl)imino-3-O-[(1R)-1-carboxy]ethyl-1,2,5-trideoxy-D-glucitol
Conditions | Yield |
---|---|
Stage #1: 2-acetamido-4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-glucitol With sodium hydride In tetrahydrofuran; oil at 60℃; for 0.5h; Inert atmosphere; Stage #2: (S)-2-chloropropanoic acid In tetrahydrofuran; oil at 20 - 60℃; for 21h; | 91% |
4-nitro-phenol
(S)-2-chloropropanoic acid
R-(+)-2- (4-nitrophenoxy) propionic acid
Conditions | Yield |
---|---|
Stage #1: 4-nitro-phenol With sodium hydroxide In water at 75℃; for 0.5h; pH=13; Stage #2: (S)-2-chloropropanoic acid In water at 75℃; for 2h; Temperature; pH-value; | 90.9% |
(S)-2-chloropropanoic acid
Benzyl 3-O-(D-1-carboxyethyl)-2-deoxy-4,6-O-isopropylidene-2-(2-tetradecylhexadecanoylamino)-α-D-glucopyranoside
Conditions | Yield |
---|---|
With sodium hydride In 1,4-dioxane 1.) 90 deg C, 1 h, 2.) 60 deg C, 5 h; | 88% |
Conditions | Yield |
---|---|
Stage #1: (S)-2-chloropropanoic acid With trichloroacetonitrile; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: C25H27NO4 With methyloxirane In tetrahydrofuran | 88% |
(S)-2-chloropropanoic acid
Conditions | Yield |
---|---|
Stage #1: (2S,4aR,7R,8R,8aS)-7-azido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: (S)-2-chloropropanoic acid With hydrogen In N,N-dimethyl-formamide; mineral oil for 0.5h; Stage #3: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 16h; | 88% |
3,4-di-O-benzyl-2-acetamido-2-desoxy-α-benzyl-D-glucopyranoside
(S)-2-chloropropanoic acid
benzyl 2-acetamido-3,4-di-O-benzyl-6-O-(D-1-carboxyethyl)-2-deoxy-α-D-glucopyranoside
Conditions | Yield |
---|---|
With sodium hydride In 1,4-dioxane at 65℃; for 1h; | 87% |
(S)-2-chloropropanoic acid
allyl 2-acetamido-2,4-dideoxy-4-fluoro-6-O-benzyl-α-D-glucopyranoside
2-N-acetyl-1-α-allyl-6-O-benzyl-4-deoxy-4-fluoro-muramic acid
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 40℃; for 18h; | 87% |
(S)-2-chloropropanoic acid
N-Pmb-L-Orn(Z)-OMe
N-[(S)-2-chloropropionyl]-N-(p-methoxybenzyl)-L-orn(Z)-OMe
Conditions | Yield |
---|---|
Stage #1: (S)-2-chloropropanoic acid With trichloroacetonitrile; triphenylphosphine In tetrahydrofuran at 0℃; for 0.5h; Stage #2: N-Pmb-L-Orn(Z)-OMe With methyloxirane In tetrahydrofuran for 48h; | 87% |
(S)-2-chloropropanoic acid
N-p-propoxybenzyl-L-Phe-OMe
N-[(S)-2-chloropropionyl]-N-p-propoxybenzyl-L-Phe-OMe
Conditions | Yield |
---|---|
Stage #1: (S)-2-chloropropanoic acid With trichloroacetonitrile; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: N-p-propoxybenzyl-L-Phe-OMe With methyloxirane In tetrahydrofuran | 87% |
(S)-2-chloropropanoic acid
N-((4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide
(R)-2-(((4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanoic acid
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20 - 50℃; for 18h; Inert atmosphere; | 85% |
With sodium hydride 1) THF, 2) 50 deg C, 18 h; Yield given. Multistep reaction; |
(S)-2-chloropropanoic acid
N-phenethyl-L-Phe-OMe
N-[(S)-2-chloropropionyl]-N-phenethyl-L-Phe-OMe
Conditions | Yield |
---|---|
Stage #1: (S)-2-chloropropanoic acid With trichloroacetonitrile; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: N-phenethyl-L-Phe-OMe With methyloxirane In tetrahydrofuran | 85% |
(S)-2-chloropropanoic acid
N-((1R,2S,3R,4R,5R)-3-hydroxy-2-(trityloxy)-6,8-dioxabicyclo[3.2.1]octan-4-yl)acetamide
Conditions | Yield |
---|---|
Stage #1: N-((1R,2S,3R,4R,5R)-3-hydroxy-2-(trityloxy)-6,8-dioxabicyclo[3.2.1]octan-4-yl)acetamide With sodium hydride In 1,4-dioxane; mineral oil at 20 - 45℃; for 0.416667h; Inert atmosphere; Stage #2: (S)-2-chloropropanoic acid In 1,4-dioxane; mineral oil at 90℃; for 1.5h; Inert atmosphere; | 85% |
Stage #1: N-((1R,2S,3R,4R,5R)-3-hydroxy-2-(trityloxy)-6,8-dioxabicyclo[3.2.1]octan-4-yl)acetamide With sodium hydride In 1,4-dioxane; mineral oil at 45℃; for 0.166667h; Stage #2: (S)-2-chloropropanoic acid In 1,4-dioxane; mineral oil at 90℃; for 0.5h; diastereoselective reaction; | 70% |
(S)-2-chloropropanoic acid
Conditions | Yield |
---|---|
Stage #1: ethyl ((4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)-1,4-dioxaspiro[4.5]decane-2-carboxamide With sodium hydride In 1,4-dioxane; mineral oil at 95℃; for 1h; Stage #2: (S)-2-chloropropanoic acid In 1,4-dioxane; mineral oil at 65℃; for 17h; | 85% |
(S)-2-chloropropanoic acid
Benzyl 2-deoxy-4,6-O-isopropylidene-2-(tetracosanoylamino)-α-D-glucopyranoside
Benzyl 3-O-(D-1-carboxyethyl)-2-deoxy-4,6-O-isopropylidene-2-(tetracosanoylamino)-α-D-glucopyranoside
Conditions | Yield |
---|---|
With sodium hydride In 1,4-dioxane 1.) 90 deg C, 1 h, 2.) 60 deg, 5 h; | 84% |
(S)-2-chloropropanoic acid
benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside
Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-<(R)-1-carboxyethyl>-α-D-glucopyranoside
Conditions | Yield |
---|---|
With sodium hydride In 1,4-dioxane at 60℃; for 0.833333h; | 84% |
(S)-2-chloropropanoic acid
allyl 2-N-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
2-N-acetyl-1-β-O-allyl 4,6-O-isopropylidenemuramic acid
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 20h; Heating; | 84% |
The Molecular Structure of (S)-(-)-2-Chloropropionic acid (CAS NO.29617-66-1):
Empirical Formula: C3H5ClO2
Molecular Weight: 108.5236
CAS registry number: 29617-66-1
Appearance: Colourless Oil
IUPAC Name: (2S)-2-chloropropanoic acid
Nominal Mass: 108 Da
Average Mass: 108.5236 Da
Monoisotopic Mass: 107.997807 Da
Index of Refraction: 1.441
Molar Refractivity: 22.31 cm3
Molar Volume: 84.4 cm3
Surface Tension: 37.6 dyne/cm
Density: 1.285 g/cm3
Flash Point: 68.1 °C
Enthalpy of Vaporization: 46.87 kJ/mol
Boiling Point: 189 °C at 760 mmHg
Vapour Pressure: 0.26 mmHg at 25°C
InChI
InChI=1/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6)/t2-/m0/s1
Smiles
C([C@@H](Cl)C)(O)=O
Synonyms: (2S)-Chloropropanoic acid ; (S)-2-Chloropropanoic acid ; (S)-2-Chloropropionic acid ; 2(S)-Chloropropionic acid ; L-2-Chloropropanoic acid ; L-2-Chloropropionic acid ; alpha-L-Chloropropionic acid ; Propanoic acid, 2-chloro-, (S)- ; Propionic acid, 2-chloro-, L- (8CI)
Product Categories: Chiral Compounds;chiral;Miscellaneous Reagents;Building Blocks for Liquid Crystals;Carboxylic Acids (Chiral);Chiral Building Blocks;Chiral Compounds (Building Blocks for Liquid Crystals);Functional Materials;Synthetic Organic Chemistry
(S)-(-)-2-Chloropropionic acid (CAS NO.29617-66-1) is used in the synthesis of muramic acid derivatives; Preparation of its ester and reaction with protected amino acid CESIUM salts to depsipeptides.
1、RTECS#: CAS# 29617-66-1: UA2451950
2、LD50/LC50: RTECS: Not available.
3、Carcinogenicity: (S)-(-)-2-Chloropropionic Acid - Not listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65.
4、Other: See actual entry in RTECS for complete information.
Hazard Codes: C
Risk Statements: 21/22-35
R21/22: Harmful in contact with skin and if swallowed
R35: Causes severe burns
Safety Statements: 23-26-28-36/37/39-45
S23: Do not breathe vapour
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S28: After contact with skin, wash immediately with plenty of soap-suds
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2511 8/PG 3
WGK Germany: 1
RTECS: UA2451950
HazardClass: 8
PackingGroup: III
HS Code: 29159080
(1)Fire Fighting Measures of (S)-(-)-2-Chloropropionic acid (CAS NO.29617-66-1):
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use foam, dry chemical, or CARBON dioxide
(2)Handling and Storage of (S)-(-)-2-Chloropropionic Acid
Handling: Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage: Store in a cool, dry place. Store in a tightly closed container. Corrosives area.
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